Advice For The Sexy Masses - A little role reversal...

Dear Kat,

I'm so shy, I don't know how to ask this, but...well, I've always wanted to penetrate my boyfriend but he's really homophobic. We experiment with a lot of things, but I'm scared of how he will react to me wanting to wear a strap on so that I can penetrate him. Should I keep it to myself or try to talk to him about it? How do you suggest I do that?

Thanks for listening to me.

Sincerely,

Shy & Scared

Dear Shy & Scared,
Nothing frustrates me more than men who think that anything that has to do with their asses is gay! I will never understand how a woman touching a man's asshole is gay. She's a woman! Not to mention the implicit suggestion that there's something wrong with homosexuality to begin with.

Anyway, I can understand your frustration. As women, we are biologically structured to receive and not to give. Isn't that annoying? There's nothing wrong with wanting a little role reversal now and then!

Please don't keep your desire to yourself! It's so important to openly and freely communicate with your partner. Given that you say your boyfriend is homophobic, I would suggest first talking to him about the fact that if he's straight, he has nothing to worry about. If that's not an option, perhaps search a free porn hub like redtube.com for videos of men being pegged by women. Introduce him to the idea of his prostate. Next time you're going down on him, massage his perineum (you might have to use your knuckles to get a proper reaction). See how he likes that. I also suggest the brilliant Canadian film Young People Fucking—it has a lovely pegging scene that reminds me of your question.

Lastly, if none of these suggestions work, I would introduce a quid pro quo. Is there something he's into that you're hesitant about? Something that's on the same level as pegging (so not a threesome, but maybe something like sex in public or anal sex). This method has always worked for me—you give me something I want and you get what you want in return. And if all goes well, he'll end up loving it and you'll have found a new game to play! Good luck.

If you have sex questions that need answers, just ask! You can either send me a private message or email me at kathleendevries@live.com. All questions will be posted completely anonymously, and I will never share your information.